WATERTOWN — American Crossroads, a Republican super PAC associated with former White House policy adviser Karl Rove and Virginia Senatorial candidate Ed Gillespie, has purchased a series of attack ads against Republican congressional candidate Matthew A. Doheny set to run in New York’s 21st District ahead of the June 24 primary election.

Mr. Doheny is running against Elise M. Stefanik, a former White House policy adviser from Willsboro. Ms. Stefanik worked in the George W. Bush White House on the Domestic Policy Council staff and in the chief of staff’s office from 2006 to 2009. Mr. Rove worked as a senior adviser and deputy chief of staff in the Bush White House until 2007.

According to documents accessed through the Sunlight Foundation’s “Political Ad Sleuth,” American Crossroads purchased 53 ads at $18,600 to run in the Burlington, Vt., media market June 3 through 9.

News of the ad buy initially appeared in the National Review, which reported that American Crossroads’ total investment in the congressional district is $240,000.

The 31-second spot, titled “Mistakes,” outlines why Mr. Doheny is “unfit for Congress,” according to paperwork filed with station WCAX in South Burlington.

“Multimillionaire Matt Doheny just doesn’t learn from his mistakes,” the video begins, before trotting out several unflattering news reports. The narrator says these factors would make it a big mistake to send him to Congress.

Among the reports are that Mr. Doheny lost three elections for Congress, including a 2009 primary election. Another said that he was sued twice for not paying rent on his New York City apartment. A third said that he was charged twice with boating while intoxicated. Yet another maintains that he violated state labor laws when he refused to pay a former campaign staffer.

The ad also attributes to the Watertown Daily Times a commment that originally appeared in an analysis by a Roll Call reporter.

“The Daily Times reported Doheny is a significantly flawed candidate,” the narrator intones, citing a two-year-old blog post by former Times political reporter Brian Amaral. The post quoted a Roll Call analysis that ran April 26, 2012.

In the Roll Call post, Josh Miller wrote about the 2012 general election between Mr. Doheny and Rep. William L. Owens, D-Plattsburgh.

“Owens will face a rematch with investment banker Matt Doheny, who is a significantly flawed candidate with a lot of money,” Mr. Miller wrote.

Mr. Doheny’s campaign took issue with the Roll Call quote and the portrayal of Mr. Doheny’s track record as a political candidate.

“Matt ran and lost in two general elections in 2010 when Doug Hoffman stayed on the Conservative line and split the vote and in 2012 when he lost by less than 5,000 votes in a district Obama carried by 6 percent,” Mr. Doheny’s campaign manager David M. Catalfamo wrote in a new release Tuesday. “Matt WON the Republican Primary in 2010 and 2012.” (Emphasis Mr. Catalfamo’s.)

There was in fact no Republican primary election in 2009. The party endorsed former Assemblywoman Dierdre K. Scozzafava to run for the seat.

But Mr. Doheny’s campaign took no umbrage with the other statements. Mr. Doheny was charged with boating while intoxicated on July 10 and July 24, 2004. He told the Times that he regretted the incidents. “I’m deeply embarrassed that it happened,” he said in 2010. “I’m disappointed in my actions and disappointed as to what happened.”

Mr. Doheny also said at the time that he had been sued in 2000 and 2005 for failing to pay rent on time for two separate New York City apartments. He said he had paid the balance after receiving notice of the suits.

The state Department of Labor awarded former staffer Alicia M. Sirk $34,383 for reimbursements and unpaid wages she earned during Mr. Doheny’s 2012 campaign.

American Crossroads has ties to one of Ms. Stefanik’s supporters, billionaire hedge fund manager Paul Singer. His PAC Winning Women donated $110,000 to Ms. Stefanik’s campaign. Mr. Singer donated $250,000 to American Crossroads on March 17, according to the Federal Election Commission.

“Elise has run an issues focused, positive, grassroots campaign from day one, and will continue to do so,” Ms. Stefanik’s spokeswoman Charlotte Guyett said in an email. “She has stayed positive in her messaging, despite the Doheny campaign’s inaccurate mailings about her. As he has done in all of his previous campaigns, Matt Doheny is the only candidate in this race who has engaged in personal attacks. This group supported our opponent in the past and clearly no longer does, making this an issue for him, not us. Our campaign is about the future, not the past. Questions about outside groups’s tactics and strategy should be directed to them.”

A statement released Tuesday by American Crossroads spokesman Paul Lindsay confirmed that the ad purchase was $242,000 and announced that it will run on broadcast and cable TV in the Albany, Watertown and Burlington/Plattsburgh markets. Steven Law, the group’s president and CEO, explained the group’s rationale for airing the ad.

“Local Republicans are uniting behind Elise Stefanik as the kind of exciting, conservative leader who can win and hold this seat,” Mr. Law said. “Elise will be a champion for lower taxes, smaller government and dismantling Obamacare.”

Ms. Stefanik has been endorsed by the New York state Conservative Party, while Mr. Doheny has been endorsed by the state Independence Party. Both candidates will be on the ballot on their respective minor party lines in November, regardless of the Republican primary’s outcome.

They will face Democrat Aaron G. Woolf and Green Party candidate Matthew J. Funiciello in November.

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